HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diethyl Ether → N-2-(4-Fluorophenoxy)ethyl-2,5-Anhydro-2,5-imino-D-glucitol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diethyl Ether | HCID 3283 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 1-(2-Bromoethoxy)-4-fluorobenzene | HCID 2064171 | — |
| Reactant | (1S,2S,3S,4R)-1,4-bis(hydroxymethyl)-5-oxa-6-azabicyclo[2.1.1]hexane-2,3-diol | HCID 68719483 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | N-2-(4-Fluorophenoxy)ethyl-2,5-Anhydro-2,5-imino-D-glucitol | HCID 131718343 | — |
Reaction Steps
A solution of a compound Formula XIV (2.60 g, 0.0159 mol), 2-(4-fluorophenoxy)ethyl bromide (3.70 g, 0.0169 mol), and Na2CO3 (1.86 g, 0.0175 mol) in 11 mL of dimethylformamide was heated at 85° C. for 8 h. The solution was cooled, then treated with 250 mL of ethyl ether portion wise, and the solvent was removed. The resultant residue was diluted with chloroform, filtered, and concentrated. This crude material was chromatographed on a Waters Prep-500 HPLC (88:11:1, CHCl3 /MEOH/NH4OH) to give the product, which was recrystallized from EtOAc/hexane (3.49 g, 73%), mp 96°-98° C. (corrected). 1H NMR supported the assigned structure.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05290948 |
| Source dataset | uspto-grants-1994_03 |
| ORD ID | ord-1757e9ed497b4d66bb64231c8f0245b2 |
| Source note | uspto-grants-1994_03 |